


A Helping Hand (Oh My God, They Were Roommates)

by EllenOfOz



Category: Supernatural
Genre: Alternate Universe - College/University, Anal Sex, Blow Jobs, Castiel and Dean Winchester are Roommates, First Time, M/M, Plot What Plot/Porn Without Plot, Roommates, Sharing a Room, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-01-14
Updated: 2020-01-14
Packaged: 2021-02-27 15:48:41
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,112
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22249702
Author URL: https://archiveofourown.org/users/EllenOfOz/pseuds/EllenOfOz
Summary: Dean Winchester had only known Castiel Novak a total of five seconds before he wanted to fuck him.Dean hadn’t even wanted to have to share a room, but ever since he had kicked open the door, his hands full with a box of his textbooks for the year, and taken in the sight of Cas sitting cross-legged on his bed, broad-shouldered, eyes wide behind his thick-rimmed glasses—and he'd uttered, "Can I help you?" in that voice—Dean was lost.And now, eight whole months later, he’s sitting wide-eyed on the edge of Cas’ bed, staring at what he’s just found underneath it.He’s…he's uncovered his roomie’s porn collection.
Relationships: Castiel/Dean Winchester
Comments: 74
Kudos: 664
Collections: The Pizzaman: A Destiel Anthology





	A Helping Hand (Oh My God, They Were Roommates)

**Author's Note:**

> This story was written for the Pizza Man Anthology - a collection of Destiel stories in print. 
> 
> Big thanks go to [FoxyMoley](https://archiveofourown.org/users/foxymoley) for organising and producing the anthology, including the image in my title banner, there! I had a lot of fun being a part of it, so thank you <3

Dean Winchester had only known Castiel Novak a total of five seconds before he wanted to fuck him. 

Dean hadn’t even wanted to have to share a room, but ever since he had kicked open the door, his hands full with a box of his textbooks for the year, and taken in the sight of Cas sitting cross-legged on his bed, broad-shouldered, eyes wide behind his thick-rimmed glasses—and he'd uttered, "Can I help you?" in that voice—Dean was lost. 

And now, eight whole months later, he’s sitting wide-eyed on the edge of Cas’ bed, staring at what he’s just found underneath it. 

It’s four o’clock on Tuesday afternoon, and Dean has been doing some procrastination-driven cleaning rather than his Physics lab report. Cas isn’t exactly the tidiest of roommates, but then, the guy’s hotter than Ellen’s hottest tamale, so he gets a pass.

That is, until Dean had found a collection of candy bar wrappers scattered under Cas’ bed. He’d fumbled around under there until he’d pulled them out, stuffing the crinkly mess into their small trash can. He’d reached under again, snagging a plastic bag this time. This one was heavier—books, perhaps? He’d pulled out the standard opaque Target bag and opened it, then quickly took his hands off it and shuffled back from where it sat on the rug. 

The top magazine peeks out from the plastic, taunting him, with “Hot Stuff” written across the top in chunky cursive. 

He’s…he's uncovered his roomie’s porn collection.

It’s not just any old bunch of Hustler or Playboy, either—Dean’s pretty sure that was a guy on the front of the topmost magazine. He shouldn’t look—he should just push it back under the bed. 

He checks his watch. Cas is in class right now—he’s not due back for at least another hour. 

Dean bites on his bottom lip as he drags out the top magazine. The shirtless dark-haired man on the cover is bare-chested, but kneeling on floorboards wearing nothing but tight jeans with a sizeable bulge in the front. He smoulders at the camera, biting his bottom lip just as Dean is still doing, and the look in his dark eyes sends a pulse of arousal straight to Dean’s core. 

"Well, hello there," he murmurs, quirking a grin. 

He quickly flips to a few pages in, and catches his breath when he’s faced with a muscled Latino-looking guy, completely nude. His huge, half-hard cock hangs down, and Dean has to swallow heavily as he takes it all in, his eyes wide. 

How has he never realized Cas is gay? He’s never seen him with or heard him talk about a girlfriend _or_ boyfriend—he’s just Dean’s quiet, nerdy roommate who only leaves his room on a Friday night when Dean drags him to the campus bar. If he’d known…well, he might have turned on the charm a lot sooner. 

It looks like Cas is taking care of himself, though, judging by the half-dozen magazines he’s got tucked away in here. Dean wonders when Cas jerks off—maybe when Dean’s out with Charlie and Garth, or at class. He imagines Cas sitting just here in his boxers, flicking through the magazines the way Dean’s doing right now, maybe slowly stroking his cock…

Damn, now Dean’s really getting uncomfortable in his jeans. He reaches down to palm his crotch, groaning a little at the pressure there.

He turns a few more pages of the magazine, until he finds another model—chiselled jaw, dark hair, blue eyes. His chest is smooth and sculpted, and a trail of hair leads down to his longer-than-average dick. 

Dean glances over his shoulder at the door of his and Cas’ room, making sure it’s closed. He unbuckles his belt and pops the button on his jeans, unzipping and shimmying down so he can pull his dick free. He strokes gently a few times. He’s just taking the pressure off, that’s all. He can’t really be expected to find all this porn and be completely unaffected, can he?

Dean’s just starting to work up a steady rhythm when the door behind him clicks, and the handle turns. Dean freezes in place, hand still on his shaft, as he turns his head in horror to see Cas walking in. He’s looking down at his phone as he closes the door behind him, but then he looks up, taking in the scene, and his mouth falls open, his eyes widening behind his thick-rimmed glasses.

“Dean?” he asks, his eyes moving from Dean, to the bag of magazines still on the floor, flicking to Dean’s hand on his rock-hard cock, then back up to Dean’s face. His own face is flushed, and he has a wild look in his eyes.

Dean can’t move. He’s frozen solid with mortification, but completely unexpectedly, a thrill rushes through him at the fact that he’s been caught. He lets out a small noise involuntarily, and Cas startles, spinning around to drop his laptop bag on his desk. “I’ll just…go, should I?”

“I’m so sorry, man, I—" Dean begins, but Cas interrupts him.

“No, it’s okay. It’s okay, I didn’t hide it very well. I’ll just…leave you to it.”

 _No, no, don’t go!_ Dean takes a breath, mumbling, “I mean…you don't have to.”

Cas turns back towards him, one eyebrow raised, and Dean’s cock gives a twitch in his fist. Castiel asks, “You…you don’t want me to?”

Dean’s really not sure at this point what’s happening, but he may as well throw caution and dignity to the wind. He starts stroking along his cock again, slowly, as Cas’ eyes follow the movement. Dean watches him gulp, then straighten his glasses on his nose. 

He takes a step closer, then another, then perches on the edge of Dean’s bed, across the room from where Dean sits. 

Dean watches him nervously for a few moments, expecting him to nope out again, but his arousal spikes when Cas just watches him move his hand on his cock, his cheeks flushed and mouth slightly open. Dean has no choice but to still his hand, willing down the tight, hot feeling in his core. If Cas is gonna keep looking at him like that, all dark eyes and wild hair, this is gonna be over a lot sooner than Dean would like. He wants Cas, has for a long time, and if he plays this right, he's gonna get him. 

"C'mere," he says, and Cas' eyes snap up to Dean's, wide with surprise. He doesn't say anything, but scoots across the room to kneel on the rug beside his own bed. 

The sight of Cas kneeling there looking down at his hand on his rock hard cock is almost enough to send Dean right over the edge, but he bites his lip and squeezes his hand slightly. 

Dean asks, quietly, "You wanna touch, Cas? Or just watch me?" 

Cas hitches in a breath, his gaze full of hunger as he looks up to stare into Dean's eyes. Then he surges forward and up, grabbing the front of Dean's shirt and pulling him down until their lips meet forcefully.

And wow, Dean must have had Cas wrong this whole time, because damn, the guy can kiss. He grabs Dean around the back of his neck and licks across his lips until Dean opens to let him in, but just as Dean makes a small moan of arousal, Cas pulls back, looking back down and removing his glasses, placing them on his bedside table. 

He looks different without them, younger perhaps, but still just as hot as he sits back on his heels.

Dean pumps his length lazily again as Cas watches, and Dean’s gaze follows as Cas' tongue peeks out to wet his lips. 

He glances up again, murmuring, "May I?" in a voice that sounds completely wrecked already. When Dean nods, Castiel pushes Dean's hands away and licks a long stripe up Dean's cock with his wide, pink tongue. 

Dean gasps out, "H-holy shit, Cas!" 

Cas pulls back, horror flashing across his face. "I'm sorry. You want me to stop?" His lips are wet, his eyes dark, and he doesn't look like he could stop right now if he tried. 

Dean rushes to reassure Cas. "No, no, please…I just wasn't expecting…aaah!" Dean's words are swallowed down as Cas leans back down and takes his whole cock into his mouth, pushing Dean to the back of his warm throat. 

He pushes up and down a few times, and the wet noises and small hums he makes as he does it send Dean rushing to the edge, his muscles tightening and his breath coming in short pants. He tries to will the pleasure building in his core to chill the fuck out, but he'd already been on his way there when Cas walked in, and what had happened after is blowing any control he might have had. _Literally_. 

He gasps as Cas' dry fingers brush under his balls. "Cas? Cas, I'm gonna—"

He tries to push Cas away, but the guy just moans and thrusts Dean back into his throat, swallowing him down as Dean comes with a cry. Stars in his vision, he throws his head back, relishing the orgasm as it crackles through his body. 

As his vision clears, he takes in the sight of Cas still kneeling on the floor in front of him, amazement on his face. 

This was not at all how he intended this afternoon to go, but Cas certainly looks like he hasn't minded the interruption to his day one bit. In fact, he licks his lips and smirks as he gets to his feet, still fully clothed. He climbs onto the bed, pushing Dean back with one hand on his chest until he's lying flat on his back, Cas looming over him. He closes the distance and kisses Dean with a fiery passion that takes Dean completely by surprise. The quiet, scholarly boy is gone—and as he tastes himself on Cas' tongue, Dean realises this is a man who knows what he wants, and what he wants is Dean. 

The idea is thrilling, yet intimidating at the same time. Dean has wanted this for such a long time that the thought of screwing it up, of having to still share a room if it all goes south, makes him pull back, detaching Cas' tongue from his mouth. 

Cas lifts his head, a little bewildered by Dean’s interruption. 

“Stop, stop,” Dean gasps out. “Are you sure you want this?”

"Dean, I've wanted this ever since you walked into this room in September. If I'd known you were queer I might have made a move sooner."

"I'm bi," Dean blurts out, cursing himself for an idiot. _Smooth, Winchester_. 

"I gathered. And now, if you don't mind, I'd like to undress you properly, open you up, and fuck you into this mattress."

Dean's brain turns to static as he stares at Cas' earnest expression, his dick making a valiant effort at getting hard again. 

Cas looks him carefully in the eye and asks, "Is that alright with you, Dean?"

Dean nods quickly, breathing a "Yes." 

"Have you done this before with a guy?" 

"Yes," Dean says, a little defensively, even though it's totally not true, but he's played around by himself with a dildo, and Cas doesn't need to know the details. 

Cas raises one eyebrow like he doesn't quite believe him, but as he moves back to climb off the bed, Dean asks, "Have you?" 

Cas holds out a hand to help Dean up. "Once or twice," he says, then pulls Dean's body flush to him and puts his lips back on Dean’s. 

Dean's head is spinning—how did his quiet, nerdy (hot) roomie end up being some kind of sex god? He thanks every lucky star for whoever it was in the college admin who put them in the same room together, because, _damn_. His thoughts fizzle out as Cas licks the skin under his left ear, sending a shiver down to his toes. 

Cas lifts the hem of Dean's shirt and pulls it over his head, then he stands back, looking Dean up and down. 

"C'mon, man," Dean says, suddenly feeling vulnerable. He reaches forward to tug at Cas' shirt. 

Cas allows him to pull his shirt off, then he unbuckles his own belt, shoving his jeans and boxers down over thighs that Dean has been admiring from across the room for months now. The guy is broad, built in a way that Dean’s own lanky form can’t hope to catch up to. When he stands up, Dean can't help the little groan that escapes him at the sight of Cas' thick, flushed cock. He takes him in hand, and they come together again, skin-on-skin, Cas hot in his palm, and on his mouth. 

He hitches in a breath as Cas grabs a handful of his ass, squeezing slightly, then moving around further to run his long fingers up his cleft. He lets go of Dean for just a moment, bending down to pull a tube of Astroglide from the bottom of the plastic bag, then again to fetch a condom from the drawer in his nightstand. 

“So prepared,” Dean says, smirking.

Cas raises one eyebrow as he looks up at him. “Like I said, I’ve done this once or twice before. Lie down and let me at you,” he adds as he opens the lube cap. 

Dean can’t seem to resist the command of that eyebrow, so he scrambles onto the bed on all fours, feeling oddly exposed with his ass in the air. A wet swipe of a finger up his crack brings a gasp out of him, and it isn’t long before Cas is circling his hole, dipping inside gently. 

“Fuck, Dean, look at you,” Castiel murmurs, spearing a long finger inside Dean, eliciting a wordless cry. “Gonna fill you up, just like that,” he says, adding a second finger as he stretches Dean open, his voice low and thick with want. 

"Cas, please…come on…ready for you..." Dean grits out, his hips involuntarily shoving back onto Cas' fingers. 

"That's good," Cas pants out, "because I've been wanting to fuck that tight little ass for months now." His fingers pull out of Dean, leaving a hollow ache behind, but it’s only for a few moments before Cas climbs onto his bed behind Dean and pulls his ass up, until Dean is on his knees again. 

Then Cas' hands leave his hips, and Dean swivels around to see what he's doing. Cas makes quick work of a condom wrapper, rolling it onto his hard length with what looks like a practised hand. His eyes flick up to meet Dean's, and he pauses for a moment. "If you need to stop, just tell me, okay?" 

Dean nods, overwhelmed with how caring Cas is being, even now. He's suddenly turned from quiet, gorgeous nerd to porn star, and now he’s thoughtful boyfriend as well? No way this is real. He just doesn't get to have nice things like this. He must be dreaming. 

But the dark-haired Adonis kneeling behind him and gently nudging his entrance with his huge cock says otherwise. Dean turns back to the bed and sighs as Cas runs one hand down beside his spine. He tries to relax, but when something huge pushes past his rim, he can’t help but clench hard.

Cas gasps, "Dean, you gotta relax! You're fine, I got you." 

Dean mutters, "Sorry, sorry," as Cas runs his hands up and down Dean's back again, dropping kisses in their wake. Gradually, he's able to push in, filling Dean up and up, way more than he ever thought he’d be able to take. It’s uncomfortable, and a little painful, and the idea that Cas is inside of him has him right on the edge of freaking out, but then Cas lets out a filthy groan and leans down to plant kisses across Dean’s back again, his hands running over Dean’s shoulders soothingly. 

“So tight, so good, Dean,” Cas murmurs as he readjusts his knees behind Dean. “Wanted to fuck you like this so many times…” 

Cas’ words send a thrill through Dean’s chest. He’s wanted this too, but his thoughts are short-circuited when Cas moves experimentally, just a shallow thrust in and out. A gasp escapes him, and Cas stills again, but Dean suddenly doesn’t want him to stop. “Come on, Cas. Give it to me,” he says, aware that his voice is broken and desperate, but not caring as Cas lets out a rumbling groan and starts up a rhythm, pulling out and thrusting in, hard. The slapping noise of skin against skin is obscene, and Dean fucking loves it, leaning back into each thrust and letting out a shout when Cas gets the angle just right for fireworks to explode in his vision and down his spine.

He may have only just come a few minutes ago, but when he palms at his dick it’s rock hard again. He jerks himself a few times, breathing out, “Fuck, Cas,” between his harsh panting.

“You like that, Dean? Gonna take all of it?” Cas’ rhythm falters for a moment, and a harsh cry rips out of him as he thrusts forward into Dean. Dean pulls at his own cock again, jerking it until he tips over the edge again, crying out, “Cas!” 

As Dean comes back to himself, he feels Cas slip out with an uncomfortable sensation, then he slumps over onto Cas’ bed, boneless. A few moments later Cas lies down against Dean’s back, stroking a hand down Dean’s side. He plants a kiss on Dean’s ear, and Dean turns to look at him. “That was, uh…unexpected,” he says.

Cas laughs. Deadpan, he replies, “Thanks a lot.” 

Dean attempts a recovery. “No, honestly, it was incredible. I had no idea…” 

“So you said already.” Cas gazes at Dean, that damn eyebrow raised again. “Is this going to make things weird between us? Because I can ask to shift rooms, if you—”

“No,” Dean protests, perhaps a little too quickly, because Cas quirks his lips up in a grin. “No, I’m definitely up for more of that if you are.” 

“Good,” Cas smiles one of his small, barely-there smiles that Dean loves. “Maybe later, though. I’ve got a paper due tomorrow.” He kisses Dean gently, then gets up and starts throwing clothes back on. 

Dean watches him, still glowing in the aftermath. Sharing a room suddenly doesn’t seem like such a bad deal after all.

**Author's Note:**

> Thanks for reading! 
> 
> Read more smutty one-shots in the rest of the [Pizza Man Anthology](https://archiveofourown.org/collections/ThePizzamanAnthology). 
> 
> If you enjoyed this story, would you mind sharing it?  
> [Here's a tumblr link](https://ellen-of-oz.tumblr.com/post/190248624956/a-helping-hand-oh-my-god-they-were-roommates-by),  
> Or you can [retweet this tweet](https://twitter.com/Ellen_of_Oz/status/1216937477795020801?s=19). Thanks!  
> There are also plenty more stories in the works from me, so if you enjoyed this, please subscribe.


End file.
